15 June 2026

Jet OUT Inc. | Chief Pilot

United States

Job Title: Base Chief Pilot

Location: Milwaukee, WI

Jet OUT is seeking a dedicated and professional Base Chief Pilot to join our aviation team in Milwaukee, Wisconsin. This flying leadership position reports directly to the System Chief Pilot and is responsible for providing day-to-day mentorship, operational oversight, and leadership for pilots assigned to the Milwaukee base. The ideal candidate is a credible, organized, and approachable aviation leader committed to upholding the highest standards of safety, accountability, and operational excellence.

Key Responsibilities

  • Serve as the primary point of contact and direct supervisor for Milwaukee-based flight crews.
  • Maintain operational proficiency as a CJ4 Pilot-in-Command, modeling professional standards.
  • Collaborate with the System Chief Pilot regarding base operations, staffing, scheduling, and pilot performance.
  • Ensure consistent application of company SOPs, manuals, and FAA regulatory standards.
  • Provide scheduled on-call leadership support for operational, safety, and crew readiness issues.
  • Participate in the pilot recruitment lifecycle, including interviewing, selection, and onboarding.
  • Facilitate pilot development, coaching, and regular performance evaluations.
  • Coordinate local training requirements and checking events, such as 135.293 and 135.299.
  • Manage base-level scheduling and serve as a liaison with Dispatch, the Training Manager, and other operational leaders.
  • Address disciplinary or interpersonal matters and execute safety and security initiatives at the base level.

Required Qualifications

  • Minimum of two years of experience in Part 135 and/or Part 121 operations.
  • Minimum of one year of experience as a Pilot-in-Command (PIC) in turbojet operations.
  • Airline Transport Pilot (ATP) certificate with Airplane Multi-Engine Land (AMEL) privileges.
  • Current First Class Medical Certificate.
  • Minimum of 3,500 hours total flight time.
  • Minimum of 1,500 hours multi-engine time.
  • Minimum of 500 hours turbofan time.
  • Valid driver’s license and FCC Restricted Radiotelephone Operator Permit.
  • Must reside or be willing to relocate within a one-hour drive of the Milwaukee area.
  • Strong knowledge of FAA regulations and demonstrated leadership and communication skills.

Preferred Qualifications

  • CE-525 type rating and specific Citation CJ4 operating experience.
  • 100 hours or more of experience in CE-525C aircraft.
  • Previous Part 135 PIC experience.
  • Prior experience as a check pilot, instructor, training captain, lead pilot, or assistant chief pilot.
  • International operating experience.

Benefits

  • 401K plan with company matching.
  • Comprehensive health, dental, and vision insurance.
  • Short-term and long-term disability coverage.
  • Group term life insurance and HSA options.
  • 3 weeks of PTO and designated holidays off.
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